Third Street South, Naples

Sometimes you just need to get away for the weekend. And whether your getaway is more of a vacation or a staycation in Naples, we can think of no better place to spend a few days than the beautiful historic district of Third Street South, just a few blocks from the Naples Pier beach. Nestled among the charming courtyards and fountains of this picturesque tree-lined street are chic clothing and home decor boutiques, art and antiques galleries, and upscale gift shops. And after a day of shopping, cocktails and dinner al fresco at one of several outstanding restaurants are just steps away.

Here, we’re sharing an itinerary to jump start planning for your weekend in Naples, as well as the ultimate place to stay, right in the heart of it all.

Day 1

Arrive in Naples

Lunch at The Continental

Shopping on Third Street South
Purple Poppy, Patina Collection, John Craig Clothier, Sequin

Sunset cruise on the Naples Princess or Miss Naples

Dinner at The Bevy

Late-night jazz at The Club Room

The Bevy


Day 2

Breakfast at Tony’s Off Third


Lunch at Sea Salt

Sunset at the Naples Pier

Dinner at Ridgway Bar & Grill

Naples Pier


Day 3

Ride bikes along Gordon Drive

Brunch at Jane’s Cafe on 3rd

Shopping in the Naples Design District
Republic of Decor, Summerfields, Samantha Drew

Dinner on the patio at The French


Right in the center of downtown Naples’ best shopping and dining is Third Street South, just a short walk from the beach and the iconic Naples Pier. Forget the hotel—there aren’t any on Third, anyway—and rent La Galleria Loft, a luxury penthouse with a private outdoor terrace. This spacious three-bedroom, three-and-a-half-bath apartment is perched directly above The Bevy, one of our favorite spots for dinner and a glass of wine pre- or post-sunset.

The space has been completely renovated to a designer luxury standard and features a large main living room with two smaller den/TV areas, a fully equipped kitchen with high-quality appliances, lots of space for dining and relaxing (it sleeps up to 10), and even a private hot tub on the balcony.

Explore inside:


370 12th Ave. S., Naples
Available for nightly or weekly rentals
Inquire: Online or directly with The Holiday Life (239-349-2494 or

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